Pentanitropiperidine



United States Patent PENTANITROPIPERIDINE Milton B. Frankel, Pasadena, Calif., assignor to Aerojetgeneral Corporation, Azusa, Calif., a corporation of bio N0 Drawing. Filed on. 22, 1956, Ser. No. 617,668 Claims. c1. 260493 This invention relates to a new composition of matter, 1,3,3,5,5-pentanitropiperidine having the structural formula:

and its preparation. Pentanitropiperidine possesses valuable explosive properties, equal to or better than the majority of commercial explosives now available.

This application is a continuation-in-part of my c0- pending United States patent application Serial No. 392,478, filed November 16, 1953, now abandoned.

Pentantropiperidine isprepared by reacting tetranitropiperidine with nitric acid, in accordance with the general reaction scheme set forth below:

In the preparation of the new compound of my invention, it is preferred to conduct the reaction at a temperature of about 5 0., however, both higher and lower temperature can be used if desired. In addition, it is also preferred to have a hydrophilic material such as acetic anhydride or other inorganic or organic anhydrides present during the course of the reaction to take up the water of reaction, thereby shifting the reaction closer to completion and increasing the yield.

The following example is provided to more clearly illustrate the preparation of the compound. It should be understood that this example is presented purely for purposes of illustration, and is not intended to limit the scope of the invention in any way.

EXAMPLE Preparation of 1,3,3,5,5-pentanitropiperidine A solution of 8 ml. of 100% nitric acid and 8 ml. of acetic anhydride was cooled to 5 C. and 0.4 gm. of

3,3,5,5-tetranitropiperidine was added. The solution was kept at this temperature for ten minutes and poured onto ice. The white solid was collected, washed with water, and dried to yield 0.3 gm. of product which was recrystallized from chloroformto give white needles, MP. C., I.S.='35-40 cm./2 kg.

Analysis.--Calcd. for C H N O percent C, 19.36; percent H, 1.95; percent N, 27.10. Found: percent C, 19.65; percent H, 1.96; percent N, 26.72.

3,3,5,5-tetranitropiperidine used as a starting material in this process is easily obtainable by the method disclosed in my abandoned application Serial No. 392,473, filed November 16, 1953.

The nitro compound of this invention is useful as a high explosive and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge. An example of such a missile is disclosed in United States Patent No. 2,470,162, issued May 17, 1949. One way of using the high explosive of this invention in a device such as that disclosed in United States Patent No. 2,470,162, is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed. A charge thus prepared is sufiiciently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure developed from ignition of a propellant charge, and can be caused to explode on operation of an impactor time fuse-mechanism firing a detonating explosive such as lead azide or mercury fulminate.

, I claim:

1. 1,3,3,5,5-pentanitropiperidine having the structural formula:

2. The method of preparing l,3,3',5,5-pentanitropiperidine which comprises reacting 3,3,5,5-tetranitropiperidine with nitric acid, at a temperature of about 5 C.

No references cited.

2,918,452; Patented Apr. 4, 1961 I 

1. 1,3,3,5,5-PENTANITROPIPERIDINE HAVING THE STRUCTURAL FORMULA: 